7 fab ways to do date night in Bend, Oregon

October 20th, 2016

Date nights are a rare and precious thing in my world. Between family time, my job at Visit Bend, and my not-so-secret life as a romantic comedy author, it’s tough to find free time for a bathroom break, let alone a whole date night.

But studies have shown regular date nights are crucial for any relationship, so I’m making the effort. Luckily, Bend is a great place to plan one. Or two. Or heck, a whole week of them.

The new Broom Closet Bar at McMenamins has a cozy, romantic vibe. Photo by Kathleen Nyberg

Here are seven tried-and-tested date nights to try in Bend, Oregon.

Dinner and a movie with a Bend twist

Turn your boring “dinner and a movie” habit into something magical (not to mention convenient) when you park yourself at McMenamins Old St. Francis in Downtown Bend.

The property got its start as a 1930s Catholic schoolhouse, but was transformed into a hotel, movie house, brewery, and more in 2004. A brand new renovation completed in July 2016 added two new buildings, a bunch of guest rooms, and even a new “hidden” bar, all of which are worth checking out if you haven’t been there for a while.

Start in the cozy Fireside Bar for an intimate pre-dinner drink, or head straight to the Old St. Francis Pub for dinner. You’ll find standard pub fare like pasta, burgers, and pizza, or opt for something more exotic like the poke marinated ahi (my personal fave).

With your bellies full, head for the movie theater and snag a comfy loveseat for two so you can snuggle. Don’t worry if you didn’t grab dinner first. You can order food to enjoy in the theater, including full meals or just Cajun tots and a beer.

After the show, head for the soaking pool. You and your honey will luxuriate in soft, saline water while scoping out the artwork and shimmering turquoise tile. Don’t forget to look up through the open ceiling for a glimpse of the stars.

Time for a post-soak drink? Park yourself by one of the fire pits at O’Kanes, or hunt for the elusive new Broom Closet Bar. Then retire to your room at McMenamins knowing you accomplished an entire date night without venturing more than a few hundred feet from your bed.

The Downtown get-around

Can’t decide which Bend restaurant or watering hole you want to visit? There’s no need to choose! Plan a route through Downtown Bend that lets you hit all the hot spots on your list.

Start with a happy hour drink at Dogwood Cocktail Cabin, which has some of the most unique concoctions you’ll find anywhere in town. Happy hour is also a great time to hit 5 Fusion, which boasts a menu created by Chef Joe Kim, a three-time semifinalist for the James Beard Award (sorta like the Oscars for chefs). Order an array of tasty sushi, or satisfy any non-fishy fans in the party with their filet mignon lollipops.

The balsamic grilled artichoke is a new addition to the menu at 10Below and sooooo tasty!

With your appetite whetted, head someplace you can order smaller dishes with some fun variety. I’m partial to Joolz with its unique Mediterranean fare and specially-priced menu that’s available anytime you opt to sit at the bar. The Camel Wings and the cauliflower are my personal faves.

Ready to get down? Head below street-level to The Capitol to soak up live music and a fun, funky vibe while you sip the Capitol Manhattan with blackberry and cocoa nib bourbon.

Want to keep going? There’s a terrific late-night happy hour at 10Below Restaurant & Lounge that features great deals on drinks and apps. Keep it light with their sweet cardamom pretzel with three dipping sauces, or indulge your craving for savory with their mouthwatering balsamic grilled artichoke.

Plan a picnic (even in the dead of winter!)

Date nights don’t necessarily need to take place at night. Why not plan a romantic picnic so you can savor time with your sweetie in Bend’s beautiful outdoor spaces?

A winter picnic makes a great date!

First things first: The food. Stock up on gourmet nibbles or grab-and-go eats at Newport Avenue Market. You’ll also find a terrific selection of ready-made salads and wraps right across the street at Devore’s Market.

Now you need to pick a place. If it’s warm outside, peruse this list of local parks to find the right spot. With nearly 80 parks scattered around our fair city, you can pick among cozy pocket parks, scenic riverfront locales, or a snazzy covered pavilion near a playground so you can frolic like kids after your meal.

And don’t think you have to skip the picnic just because there’s snow on the ground. Take a romantic winter Nordic skiing adventure together with the picnic goods in your backpack. Once you’ve worked up a good sweat on the trails at Virginia Meissner Sno Park, stop at one of the romantic warming huts to enjoy your meal (along with the views!)

A night under the stars

Love the idea of an al fresco outing, but you don’t feel like picking a place, rounding up gear, and driving to your destination?

One of many couples to get engaged during the Bonfire on the Snow outing with Wanderlust Tours.

Let Wanderlust Tours do the work for you! During the winter months, book their Bonfire on the Snow tour. You and a small group will join a knowledgeable naturalist guide as you hoof it through the starlit forest to an amphitheater carved in the snow. There, you’ll nibble sweet treats and sip an adult beverage as you take in the stars together. Wanderlust has had dozens of couples get engaged on this outing over the years, so if you’re thinking of popping the question, this is a fab time to do it.

In warmer months, Wanderlust Tours runs moonlight/starlight canoe tours on the High Cascade Lakes. What could be more romantic than canoodling in a canoe? Just like with the snowshoe tours, all your gear is included, along with transportation and treats.

The Old Mill stroll

One of Bend’s most vibrant shopping districts spans a scenic section of the Deschutes River. That makes the Old Mill District a terrific spot for a mid-afternoon date that can continue as late as you like.

Grab a romantic river view table at Greg’s Grill in the Old Mill District.

Seize the daylight before sunset and set out on a stroll along the Deschutes River. Make it a game to see who can spot otters, beavers, or countless birds shown in the free birding guide you can pick up in the Ticket Mill (along with free rental binoculars if you like).

When your stomach starts growling, head to Greg’s Grill or Anthony’s for a romantic riverfront dinner. If you’ve planned ahead, you can reserve a table with views of the water so you don’t have to give up a single second of sightseeing.

After dinner, stroll over to Flatbread Community Oven for a scoop of gelato and an excuse to warm your ice cream chilled hands in someone else’s back pocket. Um, preferably your loved one.

Get jazzy with your sweetheart

Full disclosure: I am not a fan of jazz music.

Blogger Tawna on a date night for Jazz at the Oxford.

But you know what? That’s never stopped me from thoroughly enjoying Jazz at the Oxford events hosted October through March in the Oxford Hotel for the last seven years.

Maybe it’s the terrific food and wine or the swanky setting, or maybe it’s the thrill of doing something a little outside my normal comfort zone. Either way, I’m not surprised the shows sell out every single season.

Which is one reason I was thrilled to learn the Riverhouse on the Deschutes just launched their own jazz series spanning October through April. This is a great chance to check out the $10-million renovation project they just completed, and to have a killer meal in the new Currents restaurant.

You can see the schedule (and learn more about their special Jazz + Ski + Stay packages) right here.

Come on baby, light my fire

Even if you don’t share my fire fanaticism, you’ve gotta admit there’s something magical and romantic about snuggling up beside crackling flames as you sip a craft beer or enjoy a romantic fireside meal.

Sipping beer by the fire at Crux Fermentation Project makes a romantic date night in any season.

Why not do a mini-tour of some of Bend’s best fireside hot spots?

Start with brunch at Jackson’s Corner Eastside, which boasts a cool patio fire feature in front of the restaurant. Cozy up together and enjoy matching bacon biscuit sandwiches and warm mugs of local tea.

After that, head for the Old Mill District to do a little shopping. You can make a fire pit pit stop (har!) at several locations including Pastini Pastaria (which boasts two vertical, standing outdoor fireplaces), Greg’s Grill (which boasts a huge outdoor fire pit that seats 20) and Anthony’s (which has three fire pits that can hold about 12 people each).

Finished shopping? Time to check out Bend’s craft beer scene with a stop or two on the Bend Ale Trail. The fire pit at Crux Fermentation Project is one of my favorites, and makes a great spot to share a taster tray. Make it a relationship-building exercise to choose your six sample beers together or try and guess what your loved one might pick.

10 Barrel has a killer fire pit as well, along with a tap list that always includes at least a couple sour beers (yum!) You can also cozy up together in the biergarten at GoodLife Brewing to share a snuggle by the fire, followed by a lively game of bocce ball.